Reaktion #53461

Reaktionsgleichung

water

tetrabutylammonium fluoride

1-benzhydryl-3-{[3-(tert-butyldimethylsiloxymethyl)phenyl](methylsulfonyl)methylene}azetidine

→

1-benzhydryl-3-[(3-hydroxymethylphenyl)(methylsulfonyl)methylene]azetidine

Ausbeute 57.8%

Lösungsmittel

tetrahydrofuran

ethyl acetate

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeclose to 20° C.
2. 2
   SonstigeThe organic phase is decanted off
3. 3
   Extraktionextracted
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   Einengenconcentrated to dryness under reduced pressure (2.7 kPa)
6. 6
   SonstigeThe residue obtained
7. 7
   Sonstigeis purified by chromatography on a silica gel column (particle size 0.04-0.06 mm, diameter 2 cm, height 30 cm), at a nitrogen pressure of 0.5 bar with a mixture of dichloromethane and ethanol (95/5 by volume) as eluent
8. 8
   Sonstigecollecting 60 cm3 fractions
9. 9
   Einengenconcentrated to dryness under reduced pressure (2.7 kPa)

Vorschrift

4 cm3 of a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran are added to a solution, cooled to 5° C., of 1.1 g 1-benzhydryl-3-{[3-(tert-butyldimethylsiloxymethyl)phenyl](methylsulfonyl)methylene}azetidine in 10 cm3 of tetrahydrofuran. The mixture is stirred for 3 hours at a temperature close to 20° C. and then taken up in 100 cm3 of ethyl acetate and twice 50 cm3 of water. The organic phase is decanted off, extracted, dried over anhydrous magnesium sulfate and concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is purified by chromatography on a silica gel column (particle size 0.04-0.06 mm, diameter 2 cm, height 30 cm), at a nitrogen pressure of 0.5 bar with a mixture of dichloromethane and ethanol (95/5 by volume) as eluent and collecting 60 cm3 fractions. Fractions 4 to 6 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 0.5 g of 1-benzhydryl-3-[(3-hydroxymethylphenyl)(methylsulfonyl)methylene]azetidine is obtained in the form of a white solid melting at 152° C. [NMR spectrum in DMSO-d6, T=300K, δ in ppm (300 MHz): 2.95 (3H, s, SCH3), 3.80 (2H, s, NCH2), 4.20 (2H, s, NCH2), 4.50 (2H, d, J=5 Hz, OCH2), 4.75 (1H, s, NCH), 5.25 (1H, t, J=5 Hz, OH), 7.20 (2H, t, J=7 Hz, 2CH arom.), 7.30 (8H, m. 8CH arom.), 7.45 (4H, d, J=7 Hz, 4 CH arom.)].

Quelle